4-Chloro-2-nitrobenzyl alcohol → (2-Amino-4-chlorophenyl)methanol

HRID 977187

Reaction equation

HRID 977187 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[H][H]>CO.[Pt]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([CH:3]=1)[NH2:10]

Participants

5

Reactant 2

HCID 899564-Chloro-2-nitrobenzyl alcoholHCID 178418361HCID 178418361, compound2×

Product 1

HCID 4134900(2-Amino-4-chlorophenyl)methanolYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-2-nitro benzyl alcohol (25.00 g) in methanol (1 ltr) under nitrogen at room temperature, was added platinum on sulfided carbon (2.5 g, 10% by wt). The reaction mixture was shaken under 50 psi of hydrogen until the theoretical uptake of hydrogen had occurred. Filtration, then removal of the solvent in vacuo afforded the desired compound as a solid (21.00 g). δ (360 MHz, DMSO-d6) 4.35 (2H, d, J=4.95 Hz, CH2OH), 5.17 (1H, t, J=4.95 Hz, CH2OH), 6.77 (1H, dd, J=7.98 Hz, J=2.18 Hz, 4-H), 7.06 (1H, d, J=2.18 Hz, 6-H), 7.18 (1H, d, J=7.98 Hz, 3-H), 8.08 (1H, bs, NH2), 8.47 (1H, bs, NH).

Workup

  1. filtrationFiltration
  2. customremoval of the solvent in vacuo

Sources & evidence

ORD record
ord-cf379bf4b10f44d29cf3b59deab7b83e
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Linked notes

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